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The Alice in Wonderland Conundrum

"One day Alice came to a fork in the road and saw a Cheshire cat in a tree. 'Which road do I take?' she asked. 'Where do you want to go?' was his response. 'I don't know,' Alice answered. 'Then,' said the cat, 'it doesn't matter.'"

Whether I am working with a family who is focused on developing and empowering their next generation, or an adviser group engaged in long-term strategic planning, the process commonly begins with envisioning the desired future-state and then developing a plan for its attainment. More colloquially...Goal Setting.

“Start with the end in mind" - Stephen Covey

Goal setting, as a deliberate exercise, is too often overlooked and under-utilized. Do not be mistaken, the families and advisers, with whom I have worked, have typically put real thought into what they would like to improve or where they would like to be in five to 10 years. However, these concepts are often in a vague and inchoate state; they are not a fully developed vision. Remember, success is not an accident. Without a rigorous process to create a crystal-clear vision of their ideal, and the ensuing plan to get there, their goals will remain aspirations instead of actualities.

The following is an excerpt from the book, "I thought of it While Riding My Bike", which is guidebook for personal/professional development and leading a more purposeful life.

Eight Keys to Achieving Your Goals:

  1. Set specific goals (What and When) Ambiguous goals are meaningless. The goal to “lose weight” is not a meaningful goal; but a goal to “lose 10 pounds in two months” is actionable. Be as specific as possible and set a timeline for achievement.

  2. State goals as a positive Try to word your goals in terms of achievement rather than weakness. By doing so, it helps you focus on success rather than failure. Positive goals lead to positive emotions and are therefore more likely to be pursued. Goals with a negative connotation are associated with negative emotions and won’t stimulate the same motivational influence of positively worded goals.

  3. Write your goals down The act of memorializing the goal through documenting it creates a deeper conviction on your part.

  4. Goals must be measurable If you can’t measure it, then how do you know if you are getting closer-to or further-away from accomplishing your goal?

  5. Goals must be realistic but challenging If you set unachievable goals you will set yourself up for failure, squashing your motivation and self-esteem. On the other extreme, if it is not challenging in the least, then there will be little satisfaction or benefit in its achievement.

  6. Set Supporting Short-Term Goals Short-term goals are a means to an end. They promote a feeling of success and achievement. Behavioral psychology tells us that people respond favorably to achievement. This fosters motivation. Motivation becomes that outside force that propels a body at rest into a body in motion.

  7. Share Your Goals Sharing your goals with friends/family/associates creates further commitment. It is far easier to abandon a New Year’s resolution if you are the only one who knows it. It becomes much more difficult when you have shared your goal with your social network. Additionally, sharing goals creates a support mechanism for you when you are feeling frustrated in your progress and becomes a valuable feedback system to help you recognize your growth.

  8. Review and Adjust Your Goals It is essential that you establish a schedule to review your progress. Put it on your calendar. Review your short-term-goals first, are you ahead of schedule, on track or behind schedule? If behind, is there something you should be doing differently? Do you need to adjust the timeline? The goal itself? This is a dynamic process. Be willing to make necessary adjustments along the way as long as you are staying true to your longer-term goals and your commitment to achieving them.


Too often, goal setting becomes a monumental undertaking. The sheer volume of works published in this area has led to it being viewed as an arduous burden. As you can see from the eight-steps above, it does not need to be so.

If you would like to learn more about how we can help you to create more clarity around your vision and develop actionable steps to achieving that vision, please click here.


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